CN102898504B - Antioxidation active synthetic peptide and purpose thereof - Google Patents
Antioxidation active synthetic peptide and purpose thereof Download PDFInfo
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- CN102898504B CN102898504B CN201210407446.7A CN201210407446A CN102898504B CN 102898504 B CN102898504 B CN 102898504B CN 201210407446 A CN201210407446 A CN 201210407446A CN 102898504 B CN102898504 B CN 102898504B
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Abstract
The invention discloses an antioxidation active synthetic peptide and a purpose thereof. a polypeptide provided by the invention is any one of the following polypeptides 1) to 3): 1) a polypeptide shown by a sequence I in a sequence table; 2) a polypeptide shown by a sequence 2 in the sequence table; and 3) a polypeptide shown by a sequence 3 in the sequence table. According to the invention, it is proved by experiments that three polypeptides with antioxidation activity are synthesized; as the antioxidation peptide has the advantages of small molecular weight, high activity, easiness in artificial synthesis, low cost and so on, the antioxidation peptide can be widely applied to large-scale production in industries, such as foods, cosmetics, medicines and the like; and the antioxidation active synthetic peptide disclosed by the invention can be specifically used as an antioxidant in aspects, such as cosmetics, food healthcare products, animal feed additives, medicines and the like.
Description
Technical field
The present invention relates to biological technical field, relate in particular to a kind of anti-oxidant activity synthetic peptide and uses thereof.
Background technology
Modern free radical theory points out that free radical is the hazardous compound that body produces in oxidizing reaction, can cause the oxidative damages such as lipid, protein and the regression of DNA oxidisability, causes a series of chronic diseases such as diabetes, arteriosclerosis, cancer.In food, some nutritive ingredients can be oxidized generation hydroperoxide, reduce Food Quality, even can cause absorption person's health generation disease.Therefore, find antioxidant is one of focus of paying close attention to of people to suppress the generation of hydroperoxide always.At present, the chemosynthesis antioxidants such as BHA, BHT, PG have been widely used in food service industry to prevent the oxidation of food pessimum, still because its potential hazard has limited its range of application; Some anti-oxidation peptides have the free radical of removing, singlet-oxygen quenching, decompose hydroperoxide and suppress the effects such as lipid peroxidation because of it, and there is the features such as molecular weight is little, easy absorption, also for cosmetic industry, to suppress skin aging and makeup autoxidation.
Anti-oxidation peptide is as an important composition of antioxidant, and its correlative study is in recent years also more and more.Anti-oxidation peptide is to obtain after protein digestion, separation and purification mostly, but method cost is high, disengaging time long, quality is difficult to control, anti-oxidant activity respectively has height, thereby limited scale operation and the application of anti-oxidation peptide.And utilize quantitative structure-activity relation (QSAR) model can disclose the structure activity relationship of anti-oxidation peptide, and predict the structure of high reactivity anti-oxidation peptide.
Summary of the invention
An object of the present invention is to provide a kind of anti-oxidant activity synthetic peptide.
Polypeptide provided by the invention is following 1)-3) in any one:
1) polypeptide shown in sequence 1 in sequence table;
2) polypeptide shown in sequence 2 in sequence table;
3) polypeptide shown in sequence 3 in sequence table.
Above-mentioned three polypeptide are the scope of protection of the invention; and these several polypeptide have identical amino-acid residue; all from N-terminal, the first amino acids residue and second amino-acid residue are respectively tyrosine and proline(Pro); and all there is higher anti-oxidant activity, generally in polypeptide screening and polypeptide synthesize as one group.
Aforementioned polypeptides is the polypeptide with anti-oxidant activity; Above-mentioned anti-oxidant activity specifically by ABTS remove active, ORAC is active and/or suppress that lipid peroxidation is active to be embodied.
Another object of the present invention is to provide a kind of polypeptide solution.
Polypeptide solution provided by the invention, for being dissolved in aforementioned polypeptides the solution obtaining in alcoholic solution or acidic solution; Described alcoholic solution specifically can be concentration 50%(volumn concentration) and above aqueous ethanolic solution; Described acidic solution specifically can be the aqueous hydrochloric acid that concentration is 2-20mM.
Aforementioned polypeptides or polypeptide solution are following 1)-3) in arbitrary application in described be also the scope of protection of the invention: 1) prepare anti-oxidant activity product; 2) free radical product is removed in preparation; 3) preparation suppresses lipid peroxidation product.
In above-mentioned application, remove free radical and specifically embody by removing ABTS free radical and/or cancellation AAPH free radical in an embodiment of the present invention.
Aforementioned polypeptides or polypeptide solution are also the scope of protection of the invention in the application as in antioxidant.
Aforementioned polypeptides or polypeptide solution are also the scope of protection of the invention in the application of preparing in makeup.
Aforementioned polypeptides or polypeptide solution are also the scope of protection of the invention in the application as in Animal nutrition supplement.
Aforementioned polypeptides or polypeptide solution are also the scope of protection of the invention in the application as in food nutrition supplement.
Aforementioned polypeptides is carried out chemosynthesis by Peptide synthesizer, and synthetic peptide is passed through Mass Spectrometric Identification; Have higher ABTS remove active, ORAC is active and suppress lipid peroxidation activity.
The present invention is on the basis of research anti-oxidation peptide quantitative structure-activity relation model, dopes the sequence of high reactivity anti-oxidation peptide, carries out activity checking, the one group of structural similitude drawing, the sequence that functionally active is identical after chemosynthesis.These sequences processes are compared with protein resource storehouse, are present in natural protein sequence.Compared with the anti-oxidation peptide of preparing also separation and purification with enzymolysis process, the present invention has the feature such as high free radical scavenging activity, high anti-oxidation activity.Adopt the method for chemosynthesis to prepare these anti-oxidation peptides, functionally active is high and stable, cost is lower.
Of the present inventionly experiment showed, that the present invention synthesizes 3 polypeptide, it has anti-oxidant activity, due to this anti-oxidation peptide, to have molecular weight little, active high, is easy to synthetic, the features such as cost is low, can be widely used in the scale operation of the industries such as food, makeup, medicine; Specifically can be used as antioxidant for aspects such as makeup, health care of food product, animal feedstuff additive, medicine.In a word, the invention has the advantages that: (1) has invented the peptide sequence with high anti-oxidation activity (ABTS removing is active, ORAC is active and suppress lipid peroxidation activity) that has no report; (2) polypeptide of invention is 4 peptides, and molecular weight is little, easily absorbs.(3) anti-oxidation peptide of invention is simple in structure, and synthetic is convenient, is easy to suitability for industrialized production, in food, medicine, feed and cosmetic field, has broad application prospects.
Brief description of the drawings
Fig. 1 is the mass spectrum of anti-oxidation peptide Tyr-Pro-Tyr-Trp
Fig. 2 is the high performance liquid chromatography of anti-oxidation peptide Tyr-Pro-Tyr-Trp
Fig. 3 is the mass spectrum of anti-oxidation peptide Tyr-Pro-Trp-Tyr
Fig. 4 is the high performance liquid chromatography of anti-oxidation peptide Tyr-Pro-Trp-Tyr
Fig. 5 is the mass spectrum of anti-oxidation peptide Tyr-Pro-Phe-Trp
Fig. 6 is the high performance liquid chromatography of anti-oxidation peptide Tyr-Pro-Phe-Trp
Embodiment
The experimental technique using in following embodiment if no special instructions, is ordinary method.
Material, reagent etc. used in following embodiment, if no special instructions, all can obtain from commercial channels.
The acquisition of embodiment 1, anti-oxidant activity synthetic peptide
The synthetic of polypeptide provided by sub-photo bio Technology Co., Ltd. of BeiJing ZhongKe.The preparation of polypeptide adopts the Peptide synthesizer of Apex 396 models, synthetic by Fmoc solid-phase synthesis.Respectively according to three different peptide sequence Tyr-Pro-Tyr-Trp, Tyr-Pro-Trp-Tyr, the feature of Tyr-Pro-Phe-Trp, holds N end progressively successively amino acid to be connected by C.Start, first amino acid is connected on insoluble upholder resin by the connector of one section of acid labile.After Fmoc protecting group being removed with hexahydropyridine, the amino acid of second Fmoc protection has been connected, and method of attachment has pre-activation or " treating different things alike " etc.After target sequence connects, peptide chain wash-out from resin is obtained to crude product with TFA.The polypeptide of synthesized is through high performance liquid chromatograph purifying, and purity reaches more than 90%, and through mass spectrograph qualification structure.
The present invention provides one group of synthetic polypeptide with high anti-oxidation activity according to QSAR model, specific as follows:
Polypeptide 1:Tyr-Pro-Tyr-Trp(sequence 1);
Polypeptide 2:Tyr-Pro-Trp-Tyr(sequence 2);
Polypeptide 3:Tyr-Pro-Phe-Trp(sequence 3);
Above-mentioned 3 polypeptide are 4 peptides; And the N1 position of every polypeptide is tyrosine, N2 position is proline(Pro).
Aforementioned polypeptides can synthetic, and its mass spectrum and high performance liquid chromatography detected result are as shown in Fig. 1-6:
Fig. 1 is the mass spectrum of anti-oxidation peptide Tyr-Pro-Tyr-Trp, and mass spectrum is to be measured and obtained by the mass spectrograph of Voyager-DE PRO model, mass spectrum parameter: anodal pattern, manual collection control; Acceleration voltage is 20000V; Acquisition quality scope is 300-2000Da, and the quantity of laser projection is 50/ frequency spectrum, and laser intensity is 2753, and laser frequency is 3.0HZ.Fig. 2 is the high performance liquid chromatography of anti-oxidation peptide Tyr-Pro-Tyr-Trp, chromatographic condition: analytical column is Agela (250 × 4.6mm I.D.) C18; Detection wavelength is 220nm; Gradient is 30-45%, time 15min; Mobile phase A is 0.05%TFA+2%CH
3cN, Mobile phase B is 0.05%TFA+90%CH
3cN.；
Fig. 3 is the mass spectrum of anti-oxidation peptide Tyr-Pro-Trp-Tyr, and mass spectrum is to be measured and obtained by the mass spectrograph of Voyager-DE PRO model, mass spectrum parameter: anodal pattern, manual collection control; Acceleration voltage is 20000V; Acquisition quality scope is 300-2000Da, and the quantity of laser projection is 50/ frequency spectrum, and laser intensity is 2753, and laser frequency is 3.0HZ; Fig. 4 is the high performance liquid chromatography of anti-oxidation peptide Tyr-Pro-Trp-Tyr, chromatographic condition: analytical column is Agela (250 × 4.6mm I.D.) C18; Detection wavelength is 220nm; Gradient is 28-43%, time 15min; Mobile phase A is 0.05%TFA+2%CH
3cN, Mobile phase B is 0.05%TFA+90%CH
3cN.
Fig. 5 is the mass spectrum of anti-oxidation peptide Tyr-Pro-Phe-Trp, and mass spectrum is to be measured and obtained by the mass spectrograph of Voyager-DE PRO model, mass spectrum parameter: anodal pattern, manual collection control; Acceleration voltage is 20000V; Acquisition quality scope 300-2000Da, the quantity of laser projection is 50/ frequency spectrum, and laser intensity is 2753, and laser frequency is 3.0HZ.Fig. 6 is the high performance liquid chromatography of anti-oxidation peptide Tyr-Pro-Phe-Trp, chromatographic condition: analytical column is Agela (250 × 4.6mm I.D.) C18; Detection wavelength is 220nm; Gradient is 28-48%, time 20min; Mobile phase A is 0.05%TFA+2%CH
3cN, Mobile phase B is 0.05%TFA+90%CH
3cN; The concrete outcome of Fig. 6 is as following table 1:
Table 1 is the high performance liquid chromatography result of anti-oxidation peptide Tyr-Pro-Phe-Trp
The activity of embodiment 2, anti-oxidant activity synthetic peptide detects
Aforementioned polypeptides 1,2,3 is dissolved in respectively in 50% aqueous ethanolic solution, obtains polypeptide 1 solution, polypeptide 2 solution, polypeptide 3 solution, mother liquid concentration is 10mM, is then diluted to desired concn below with deionized water.
1, measure the ABTS removing activity of anti-oxidation peptide by TEAC method
The Potassium Persulphate hybrid reaction that is 2.45mmol/L by 7mmol/L ABTS (aqueous solution) and final concentration produces ABTS
+, mixed solution, at the lower 16h that places of dark room temperature (25 DEG C), obtains ABTS
+solution.ABTS
+solution dilutes with dehydrated alcohol, and extremely the light absorption value under 734nm is 0.7 ± 0.02.Get this solution 4ml and mix with the polypeptide solution to be measured of 40 μ l0.5mM, under 734nm, measure absorbancy at 30 DEG C, replace sample as blank with distilled water, test parallel 3 times.Adopting serial Trolox(Chinese name: watermiscible vitamin E) solution replaces polypeptide solution to be measured, drawing standard curve after measuring.Result is expressed as the concentration of the needed Trolox of resistance of oxidation that polypeptide solution to be measured is suitable.ABTS
+the calculation formula of clearance rate is as follows:
In formula: A
0for blank sample is in the absorbancy at 734nm wavelength place; A treats the absorbancy of test sample at 734nm wavelength place.Result is expressed as the micro-molar concentration of the resistance of oxidation needed Trolox suitable with the testing sample of every micro-molar concentration.
Result is as follows: the ABTS clearance rate of peptide T yr-Pro-Tyr-Trp, Tyr-Pro-Trp-Tyr and Tyr-Pro-Phe-Trp is respectively 79.80%, 79.88% and 64.95%, activity value be respectively 4.09,4.09 and 3.33(μ mol/ μ mol); Higher than the positive control vitamins C (VC) under equal conditions and gsh (GSH) level, (clearance rate is respectively 14.55% and 30.03%; Activity value is 0.76 and 1.55).
Illustrate that aforementioned polypeptides all has higher anti-oxidant activity.
2, measure the anti-oxidant activity value of anti-oxidation peptide by ORAC method
Based on ORAC, reaction is carried out in 75mM potassium phosphate buffer (pH=7.4) environment, and fluorescent agent FL is mixed with high density storing solution with this damping fluid, and after small volume packing, 4 DEG C of preservations, can store 4 weeks.When experiment, take out necessary amount and be diluted to final concentration in reaction system as 70nM taking same 75mM potassium phosphate buffer.AAPH prepares to reaction system final concentration as 12mM and uses taking 75mM potassium phosphate buffer.Standard antioxidant Trolox and testing sample also all dissolve and dilution with damping fluid.AAPH and Trolox matching while using.
Concrete measurement operation is, in the each micropore of 96 orifice plate, add respectively and add FL120 μ L after 5 μ M polypeptide solution 20 μ L to be measured at 37 DEG C after preset 12min, in each hole, adding rapidly AAPH 60 μ L to start with multichannel pipettor reacts, and by microwell plate be placed in fluorescence analyser at 37 DEG C with excitation wavelength 485nm, emission wavelength 520nm, carry out METHOD FOR CONTINUOUS DETERMINATION, every 1min measures once each hole fluorescence intensity, and minute is 2h.
ORAC experiment need to be set two kinds of contrasts, the Free Radical contrast (+AAPH) when not adding the FL fluorescence Natural Attenuation contrast (AAPH) of free radical and thering is no antioxidant.The resistance of oxidation of sample and fluorescence decline curve under Free Radical to delay part area (NetAUC) directly related.
Area poor under the fluorescence decline curve of area Free Radical when existing without antioxidant under fluorescence decline curve under antioxidant action, the protected area that the decay part area Net AUC of fluorescence quenching curve is antioxidant.
AUC=1+(f
1/f
0+f
2/f
0+f
3/f
0+……+f
n/f
0)
Wherein f
0fluorescent value reading while referring to start; f
nrefer to the fluorescent value reading in the time of n min.
Net AUC=AUC
antioxidant-AUC
contrast
Net result is expressed as the micro-molar concentration of the needed Trolox of resistance of oxidation that the polypeptide solution to be measured of every micro-molar concentration is suitable.
Result be the ORAC activity value of antioxidation polypeptide Tyr-Pro-Tyr-Trp, Tyr-Pro-Trp-Tyr and Tyr-Pro-Phe-Trp be respectively 5.61,4.90 and 3.63(μ mol Trolox/ μ mol), be respectively 0.63 and 1.11 higher than the positive control VC under equal conditions and GSH(ORAC activity value).
Illustrate that aforementioned polypeptides all has higher anti-oxidant activity.
3, thiocyanate-ferric (FTC) is measured the inhibition lipid peroxidation activity of anti-oxidation peptide
In 5mL tool plug test tube, add 0.5mL distilled water, the linolic acid emulsion of 2.5mL 20mM (mixes 0.2804g linolic acid with 0.2804g polysorbas20, add again 50mL0.1MpH7.0 phosphoric acid buffer), the phosphoric acid buffer (pH7.0) of 2mL0.1mol/L, add 0.5mL5mM polypeptide solution to be measured in glass test tube, total reaction volume 5.5mL.After mixing, place in 50 DEG C of lucifuges.Replace polypeptide solution to be measured as negative control with ethanol, be dissolved in 99.5% ethanol with BHT and VE() positive contrast.
(0h, 2h, 4h, 6h, 8h, 12h, 24h, 30h, 36h, 48h) draws 100 μ L mixed solutions and joins in the ethanolic soln of 4.7mL75% from above-mentioned tool plug test tube at set intervals, add again the ammonium thiocyanate solution of 100 μ L 30% (g/g), iron protochloride hydrochloric acid (3.5%) solution of 100 μ L 20mmol/L.Reaction 3min then measures light absorption value under 500nm.Light absorption value reaches 0.3 number of days as inductive phase.Anti-oxidant activity is expressed as the inductive phase of sample divided by the inductive phase of positive control relatively.
Result is that the lipid peroxidation inhibiting rate of antioxidation polypeptide Tyr-Pro-Tyr-Trp, Tyr-Pro-Trp-Tyr and Tyr-Pro-Phe-Trp is respectively 66.34%, 68.11% and 63.21%, and its relative anti-oxidant activity is 4.55,5.42 and 3.69.Higher than the vitamin-E under equal conditions (VE) (inhibiting rate is 61.18%).
Illustrate that aforementioned polypeptides all has higher anti-oxidant activity.
The application of embodiment 3, anti-oxidation peptide
1, anti-oxidation peptide adds in makeup rich nourishing cream as antioxidant component
Rich nourishing cream (massfraction %)
Above-mentioned anti-oxidation peptide can be any one in 3 anti-oxidation peptides that obtained by embodiment 1.
Result anti-oxidation peptide, because molecular weight is little, can be absorbed by the skin fast, can delay skin aging.
2, anti-oxidation peptide joins in facial mask as antioxidant component
Skin cleaning mask formula (massfraction %):
All the other are water
Above-mentioned anti-oxidation peptide can be any one in 3 anti-oxidation peptides that obtained by embodiment 1.
Result anti-oxidation peptide has the effect of removing free radical, preventing color spot.
3, anti-oxidation peptide joins in cat grain with nutritious supplementary as animal
Cat grain formula is as follows: main batching has chicken, pork, the flesh of fish (weight 50%); Rice, corn, vegetable fibers, iodized salt, vegetables oil and animal tallow, nutritious supplementary etc.Component list: crude protein (at least) 31%, crude fat (at least) 9%, fiber (at the most) 130 mg/kg, moisture content (at the most) 10%, ash (at the most) 8%, salt (at the most) 0.5%, anti-oxidation peptide 2%.
Above-mentioned anti-oxidation peptide can be any one in 3 anti-oxidation peptides that obtained by embodiment 1.
Result anti-oxidation peptide can supplement amino acid can supplement again antioxidant, can play in vivo the effect of removing free radical and delaying senility.
4, anti-oxidation peptide joins in soy sauce batching as food enrichment.
Raw sauce 6%
Caramel colorant 0.06%
Sodium-chlor 2%
Monosodium glutamate 0.7%
Lactic acid 0.06%
Sanitas 0.02%
Anti-oxidation peptide 0.05%
Above-mentioned anti-oxidation peptide can be any one in 3 anti-oxidation peptides that obtained by embodiment 1.
Result anti-oxidation peptide can supplement amino acid can supplement again antioxidant, can play in vivo the effect of removing free radical and delaying senility.
Claims (7)
1. a peptide species is the polypeptide shown in sequence in sequence table 2.
2. polypeptide according to claim 1, is characterized in that: described polypeptide is the polypeptide with anti-oxidant activity.
3. a polypeptide solution, for being dissolved in polypeptide described in claim 1 or 2 solution obtaining in alcoholic solution or acidic solution.
Described in claim 1 or 2 polypeptide or polypeptide solution claimed in claim 3 following 1)-3) and in arbitrary application in described:
1) prepare anti-oxidant activity product;
2) free radical product is removed in preparation;
3) preparation suppresses lipid peroxidation product.
5. polypeptide or polypeptide solution claimed in claim 3 application in preparation Animal nutrition supplement described in claim 1 or 2.
6. polypeptide or polypeptide solution claimed in claim 3 application in preparation food nutrition supplement described in claim 1 or 2.
Described in claim 1 or 2 polypeptide or polypeptide solution claimed in claim 3 in the application of preparing in makeup.
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| CN109311945A (en) * | 2016-03-02 | 2019-02-05 | Cue生物制药公司 | T cell modulability multimeric polypeptide and its application method |
| KR20180132070A (en) * | 2016-03-03 | 2018-12-11 | 큐 바이오파마, 인크. | T-cell modulated multimeric polypeptides and methods for their use |
| CN106093374B (en) * | 2016-06-03 | 2017-08-22 | 广州市进德生物科技有限公司 | A kind of one-component TMB nitrite ions and preparation method thereof |
| CN106749525B (en) * | 2016-12-07 | 2020-01-07 | 南京财经大学 | Small peptide and application thereof |
| CN107467372A (en) * | 2017-07-31 | 2017-12-15 | 兰溪市酉泽饲料技术服务有限公司 | The preparation method of fancy carp adult fish phase feed |
| CN107467412A (en) * | 2017-07-31 | 2017-12-15 | 兰溪市酉泽饲料技术服务有限公司 | The preparation method of snakehead adult fish phase feed |
| CN107467371A (en) * | 2017-07-31 | 2017-12-15 | 兰溪市酉泽饲料技术服务有限公司 | The preparation method of Crucian carp fingerlings phase feed |
| CN107397084A (en) * | 2017-07-31 | 2017-11-28 | 兰溪市酉泽饲料技术服务有限公司 | The preparation method of snakehead young stage feed |
| CN107383167B (en) * | 2017-08-07 | 2021-02-09 | 温州千瑞生物科技有限公司 | Antioxidant active peptide and application thereof |
| CN108308377A (en) * | 2018-01-08 | 2018-07-24 | 佛山市所能网络有限公司 | A kind of feed for pet and preparation method thereof with anti-oxidation health effect |
| CN115444101A (en) * | 2022-09-09 | 2022-12-09 | 中国人民解放军陆军勤务学院 | Method for prolonging shelf life of instant brewing rice |
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| JP5582433B2 (en) * | 2009-03-24 | 2014-09-03 | 国立大学法人名古屋大学 | Method for extracting rule representing functional peptide, method for designing and preparing functional peptide, method for evaluating polypeptide or polypeptide-containing composition, and functional peptide |
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